This invention generally pertains to a heterocyclic carbon compound having drug and bio-affecting properties and to its preparation and use. In particular, the invention is concerned with the S-oxide derivative of an antipsychotic benzisothiazole piperazine compound.
In U.S. Pat. No. 4,411,901, issued Oct. 25, 1983, and a related divisional, U.S. Pat. No. 4,452,799, issued June 5, 1984; Temple, et al., disclosed a series of benzisothiazole and benzisoxazole piperazine derivatives having selective antipsychotic activity. A preferred compound of this series, designated BMY 13859, has the structure shown below as 1. ##STR1## BMY 13859 is currently being evaluated clinically and appears to be a promising antipsychotic agent.
The compound representing the present invention is the sulfoxide derivative of BMY 13859 and is designated BMY 20366. Of additional interest, metabolic interconversion appears to occur between BMY 13859 and the compound of the instant invention. Metabolic interconversion of sulfides and sulfoxides is known, with the biotransformations of sulindac (2) being reported by Kwan and Heimlich, Internat. J. of Pharmaceutics, 6, (1980) 237-241. ##STR2## For sulindac, the pharmacological activity appears to reside only in the sulfide metabolite, which distinguishes sulindac from the instant sulfoxide compound. The instant compound, BMY 20366, appears to be a selective antipsychotic agent possessing a different in vitro binding profile compared with BMY 13859. Expression of pharmacological activity by BMY 20366, the sulfoxide derivative of BMY 13859 would not be obvious from the sulindac art.